(S)-4-(2-chloro-9-methyl-6-(3-methylmorpholino)-9H-purin-8-yl)tetrahydro-2H-pyran-4-ol → (S)-4-(2-chloro-9-ethyl-6-(3-methylmorpholino)-9H-purin-8-yl)tetrahydro-2H-pyran-4-ol

HRID 2063371Notes

Reaction equation

HRID 2063371 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:12]3([OH:18])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[N:8]2[CH3:11])=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]2[CH3:25])[N:3]=1.Cl[C:27]1N=C2C(N=CN2CC)=C(N2CCOC[C@@H]2C)N=1>>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:12]3([OH:18])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[N:8]2[CH2:11][CH3:27])=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]2[CH3:25])[N:3]=1

Participants

3

Reactant 2

HCID 58222532(S)-4-(2-chloro-9-methyl-6-(3-methylmorpholino)-9H-purin-8-yl)tetrahydro-2H-pyran-4-olHCID 58222539(S)-4-(2-chloro-9-ethyl-9H-purin-6-yl)-3-methylmorpholine

Product 1

HCID 58222538(S)-4-(2-chloro-9-ethyl-6-(3-methylmorpholino)-9H-purin-8-yl)tetrahydro-2H-pyran-4-ol

Procedure

This compound (g-1) was prepared in an analogous fashion to (S)-4-(2-chloro-9-methyl-6-(3-methylmorpholino)-9H-purin-8-yl)tetrahydro-2H-pyran-4-ol, using (S)-4-(2-chloro-9-ethyl-9H-purin-6-yl)-3-methylmorpholine as the starting material. 1H NMR (CDCl3, 400 MHz) δ ppm 5.65 to 4.75 (broad d, 2H), 4.46 (q, 2H), 4.05 to 3.85 (m, 5H), 3.83 to 3.73 (m, 2H), 3.62 (dt, J=11.6 Hz, 2.6 Hz, 1H), 3.55 to 3.39 (broad s, 1H), 2.59 (s, 1H), 2.46 to 2.34 (m, 2H), 1.87 (d, J=12.8 Hz, 2H), 1.45 (t, J=7.2 Hz, 3H), 1.40 (d, J=6.8 Hz, 3H); LC-MS m/z (method B2)=382/384 [M+H]+, RT=1.79 min.

Sources & evidence

ORD record
ord-0b9bf7c0da7343c1a520b6e38af1b2d4
Source dataset
uspto-grants-2012_10
Patent number
US08288381B2

Reaction notes

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